Ethyl 4-oxo-1-piperidinecarboxylate → HCID 23627925, compound

HRID 2421061Notes

Reaction equation

HRID 2421061 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]3[NH:10][C:9]2=[O:17])[CH2:4][CH2:3]1.O=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.C([O-])(=O)C.[K+].C([BH3-])#N.[Na+]>CO>[O:17]=[C:9]1[N:8]([CH:5]2[CH2:4][CH2:3][N:2]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:7][CH2:6]2)[C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[NH:10]1

Participants

6

Reactant 4

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 517044Potassium AcetateHCID 5003444Sodium cyanoborohydrideHCID 131728947HCID 131728947, compound

Product 1

HCID 23627925HCID 23627925, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis-(+/−)-1-piperidin-4-yloctahydro-2H-benzimidazol-2-one hydrochloride salt (150 mg, 0.58 mmol) in 5 mL MeOH was added ethyl 4-oxopiperidine-1-carboxylate (119 mg, 0.69 mmol) and potassium acetate (1 eq). The mixture was stirred at room temperature for 30 min and sodium cyanoborohydride (182 mg, 2.90 mmol) was added. The mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was dissolved in 20 mL DICHLOROMETHANE, and was washed with water. Organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by High pH prep-LCMS to afford the desired racemic mixture as white solid (102 mg, 46%). MS (M+1): 379.3

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 20 mL DICHLOROMETHANE
  4. washwas washed with water
  5. dry with materialOrganic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by High pH prep-LCMS

Sources & evidence

ORD record
ord-1c686374170e416480c3a33a58f0a49e
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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